The present invention relates to the use of derivatives of N-phenyl-3,4,5,6-tetrahyrophthalimide of the general formulae I and/or II 
where
R is hydrogen, fluorine or chlorine,
A is hydrogen, C1-C4cyanoalkyl or a group I-1 to I-11
R1 is hydrogen, chlorine, bromine cyano or C1-C6-alkyl,
R2 is hydrogen, C1-C8-alkyl, C1-C8-alkenyl  C2-C8-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, phenyl-C1-C3-alkyl or, where X is NR8  where Q is NR8, also C1-C4-hydroxy-alkyl, C1-C4-alkoxy, C2-C4-alkenyloxy, phenyl, phenyl substituted by halogen, C1-C4-alkyl or -alkoxy, C1-C4-haloalkyl or -haloalkoxy,
R3 is hydrogen, C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-haloalkyl, C1-C5-cyanoalkyl, C1-C4-mercaptoalkyl, C1-C4-alkoxyalkyl, C1-C4-alkylthioalkyl, C1-C4-alkylcarbonyloxy-C1-C4-alkyl or C1-C4-alkoxycarbonyl-C1-C4-alkylthioalkyl,
R4, R5 and R6 are each hydrogen or C1-C3-alkyl,
E is oxygen or methylene,
X is oxygen or sulfur,
Q is oxygen, sulfur or N8,
Y is oxygen, sulfur or CHR4,
n is 0 or 1,
Z is methylene, methyleneoxymethylene, methylenethiomethylene or ethenylene, R7 is hydrogen, C1-C6-alkyl, C1-C6-alkoxyalkyl, C1-C6-alkylthioalkyl or C5- or C6-cycloalkyl,
R8 is C1-C8-alkyl, C3-,or C4-alkenyl, C3- or C4-alkynyl or C1-C6-alkoxyalkyl,
R9 is hydrogen, chlorine, bromine, cyano, C-C4-alkyl, C3- or C4-alkenyl, C3- or C4-alkynyl, C1-C6-alkoxyalkyl, C1-C6-alkylthioalkyl or cyclohexylmethyl,
R10 is hydrogen, halogen, cyano, C1-C4-alkyl, C1-C3-alkoxycarbonyl or C1-C4-alkoxycarbonyl, or R9 and
R10 together form a C4- or C5-alkylene or C4- or C5-oxoalkylene group,
R11 is C1-C6-alkyl, C3- or C4-alkenyl, C3- or C4-alkynyl or a group 
xe2x80x83or xe2x80x94CH2C(CH3)2COOR2,
R12 is hydrogen or cyano,
R13 is hydrogen or C1-C4-alkoxycarbonyl,
R14 is C1-C4-alkyl, C3- or C4-alkenyl, C3- or C4-alkynyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, tetrahydrofurfuryl, dihydropyranylmethyl, dihydrothiopyranylmethyl, tetrahydropyranylmethyl or tetrahydrothiopyranylmethyl,
R15 is hydrogen, C1-C4-alkyl, C3- or C4-alkynyl, C1-C4-alkoxycarbonyl -C1-C4-alkyl or xe2x80x94Nxe2x95x90C(CH3)2 and
R16 is hydrogen; C1-C4-alkyl, C3- or C4-alkenyl, C3- or C4-alkynyl, unsubstituted benzyl or benzyl which is, monosubstituted to trisubstituted by halogen or C1-C4-alkyl, tetrahydrofurfuryl, dihydropyranylmethyl, dihydrothiopyranylmethyl, tetrahydropyranylmethyl or tetrahydrothiopyranylmethyl,
for the desiccation and abscission of plant organs.
The present invention furthermore relates to a method for the desiccation and abscission of plant organs, in particular of the leaves, by means of the above-mentioned compounds I and II.
EP-A 207 894 discloses that specially substituted N-phenyl-3,4,5,6-tetrahydrophthalimides have selected herbicidal properties as well as a plant growth-regulating action. An example indicates the desiccant and defoliant action in cotton plants without specifying the active ingredients. The application rates are 0.6 and 1.2 kg/ha. Evidently no good results were obtained with 0.3 kg/ha.
The use of tetrahydrophthalimide derivatives as herbicides is described in a number of publications, for example in DE-A-36 03 789, DE-A-36 07 300, DE-A-30 13 162, DE-A-31 09 035, DE-A-35 33 440, EP-A-61 741, EP-A-83 055, EP-A-68 822, EP-A-236 916, GB-A-20 71 100, U.S. Pat. No. 3,878,224, JP 59/155 358 and JP 61/027 962. These publications do not disclose the use of the compounds as abscission agents for the controlled induction of the dropping of leaves, blossoms of fruit in crops, such as cotton, citrus fruit, olives, pomes and drupes, and their use as desiccants for drying out the visible parts in crops, for example potato, rape, sunflower and soybean.
There is considerable economic interest in both abscission agents and desiccants, for facilitating harvesting. Particularly in intensive cotton cultivation, the use of defoliants is essential for effective use of picking machines or harvesting the bolls. The commercial products used to date do not meet essential requirements in practice, for example rapid and lasting activity even under cooled temperature conditions, low application rates and no environmental pollution (toxicity, odor and flammability).
We have found that the N-phenyl-3,4,5,6-tetrahydrophthalimides defined at the outset have high activity with regard to the abscission and desiccation of plant organs. Their use has considerable advantages compared with known agents:
a) Their action is optimum even at low application rates of about 60-250 g/ha,
b) Their effect is much more complete at a comparable application rate and
c) Their action is much more reliable even at low temperatures.
In addition to their excellent action as defoliants, the compounds I and/or II have very good activity when they are used as desiccants for drying out the visible parts of crop plants, for example potatoes, sunflower, soybean and rape, in order to facilitate the harvesting process. Furthermore, they result in uniform ripening of the fruit to be harvested.
The compounds which are particularly preferred because of their activity are N-phenyl-3,4,5,6-tetrahydrophthalimides of the structure I, where R is fluorine or, in particular, hydrogen.
Preferred radicals A are the following groups: 
where Q is oxygen,  R1 is H, Cl, Br, CN or C1-C6-alkyl, in particular C1-C4-alkyl, and R2 is H, C1-C8-alkyl, in particular C1-C4-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or isobutyl, C1-C8-alkenyl  C2-C8-alkenyl, in particular C1-C 4-alkenyl , C2-C4-alkenyl, C3- or C4alkynyl  C4alkynyl, C1-C8-C4-alkylthio-C1-C4-alkyl , C1-C4-alkylthio-C1-C4-alkyl, C1-C17-aralkyl, for example phenylalkyl, such as benzyl or 2-phenylethyl, or C3-C6-cycloalkyl, in particular C5- or C6-cycloalkyl, such as cyclopentyl or cyclohexyl, 
where X is O or S, n is 0 or 1, R3 is H or C1-C4-alkyl as stated for R2, which may be substituted by hydroxyl, halogen, such as fluorine, chlorine or bromine, cyano, mercapto, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkyl-carbonyloxy or C1-C4-alkoxycarbonyl-C1-C4-alkylthio, and R4 is hydrogen or C1-C3-alkyl,
OR14xe2x80x83xe2x80x83( I-10
where R14 is, in particular, tetrahydrofurfuryl, dihydropyranylmethyl, dihydrothiopyranylmethyl, tetrahydropyranylmethyl or tetrahydrothiopyranylmethyl.
The N-substituted tetrahydrophthalimides I are obtainable from 3,4,5,6-tetrahydrophthalic anhydride and appropriately substituted aniline derivatives, which can be prepared by reduction of the corresponding nitro compounds. As a rule, the reaction is carried out in an inert solvent at from 20xc2x0 to 200xc2x0 C., preferably from 40xc2x0 to 50xc2x0 C. Examples of suitable solvents are lower alkanecarboxylic acids, such as glacial acetic acid or propionic acid, or aprotic solvents, such as toluene or xylene, in the presence of acidic catalysts, for example aromatic sulfonic acids.
Cyanoalkyl-substituted N-phenyltetrahydrophthalimides are described in EP-A 68 822.
N-phenyltetrahydrophthalimides in which A is a group I-1 are disclosed in DE-A 36 03 789 (EP-A 240 659) or DE-A 37 24 399 (EP-A-300 387). They can also be prepared by reacting an aldehyde of the formula IV 
with a phosphorane of the formula V 
where Ar is unsubstituted or substituted phenyl at from xe2x88x9210xc2x0 to 100xc2x0 C. and in the presence of a solvent. The aldehydes of the general formula IV which are used as starting materials are obtainable in a simple manner by the methods described in German Patent Application 3815042.5 (0.Z. 0050/39993). The radical R of these compounds may be hydrogen or fluorine.
The phosphoranes V which are required for the preparation of the tetrahydrophthalimides and which are also referred to as phosphorylides are obtainable by methods known from the literature (for example Houben-Weyl, Methoden der Organischen Chemie, Vol. E1, pages 636-639, Georg-Thieme Verlag, Stuttgart 1982).
The reaction of the starting compounds IV and V is in general advantageously carried out in the presence of a solvent. Suitable solvents are all solvents conventionally used for carrying out Wittig reactions, for example halogenated solvents, such as chloroform, or ethers, such as tetrahydrofuran, dioxane or ethylene glycol dimethyl ether. Preferred solvents are alcohols, in particular C1-C4-alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol or tertbutanol. The solvents can also be used in the form of solvent mixtures but as a rule the pure solvents are preferably employed. If alcohols are used as solvents, it is generally advantageous to use as a solvent that alcohol which corresponds to the alcohol component of the ester group in I and V.
Of course, the optimum reaction temperature depends on the particular starting compounds IV and V to be reacted and on the solvent used. In general, however, the reaction is carried out at from xe2x88x9210xc2x0 to 100xc2x0 C., preferably from xe2x88x9210xc2x0 to 60xc2x0 C., particularly advantageously from 10xc2x0 to 40xc2x0 C.
The starting compounds IV and V can be reacted with one another in stoichiometric amounts. However, it may prove advantageous if one of the two reactants, IV or V, is used in the reaction in a molar excess of from 10 to 20%.
N-phenyltetrahydrophthalimides in which the Group A is I-2 or I-3 are described in German Applications P 37 41 272.8 and P 37 41 273.6. Compounds in which A is I-4 or I-5 are disclosed in DE-A-36 03 789 (EP-A-240 659). N-phenyltetrahydrophthalimides in which A is I-6 and I-7 are described in German Applications P 37 41 272.8 and P 38 19 464.3. Compounds I in which A is I-8 and I-9 are disclosed in DE-A-37 24 395 (EP-A-300 398) and 36 07 300 (EP-A-236 916). Compounds I in which A is I-10 are described in German Application P 37 36 297.6. Compounds I in which A is I-11 are disclosed in DE-A-31 09 035 and 35 33 440 and in GB-A-20 71 100.
N-aryltetrahydrophthalimide compounds of the structure II can be obtained by reacting a correspondingly substituted amine III 
with an N-alkylating compound Z-R16, where Z is an acid radical which initiates N-alkylation, and reacting the resulting amine in a conventional manner with tetrahydrophthalic anhydride. It is also possible first to carry out the reaction of III with tetrahydrophthalic anhydride and then to effect N-alkylation. Preferred alkylating agents are halogen compounds, tosylates or mesylates of the radicals to be introduced. The preparation of compounds of the structure II is described in, for example, German Application P 38 07 295.5.
The active ingredients I and/or II may be used, for example, in the form of directly sprayable solutions, powders, suspensions, including concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, broadcasting agents or granules, by spraying, atomizing, dusting, broadcasting or pouring. The application forms depend entirely on the intended uses; they should in any case ensure very fine distribution of the novel active ingredients.
Mineral oil fractions having a medium to high boiling point, such as kerosine or diesel oil, and coal tar oils and vegetable or animal oils, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol. butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, highly polar solvents, e.g. dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone or water, are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances as such may be dissolved in an oil or solvent and homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates which consist of active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil and which are suitable for dilution with water.
Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, ligninsulfite waste liquors and methylcellulose.
Powder, broadcasting, coated, impregnated and homogeneous granules can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths, such as silica gel, silicas, silicates talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, kieselguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal meal, ground bark, woodmeal, nutshell meal and cellulose powder, and other solid carriers.
The formulations contain from 0.1 to 95, preferably from 0.5 to 90% by weight of active ingredient.
Examples of formulations are:
I. 90 parts by weight of the compound according to Example 1.1 are mixed with 10 parts by weight of N-methyl-xcex1-pyrrolidone to give a solution which is suitable for use in the form of very small drops.
II. 20 parts by weight of the compound of Example 1.17 are dissolved in a mixture which consists of 80 parts by weight of xylene, 10 parts by weight of the adduct from 8 to 10 moles of ethylene oxide with 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely dispersing it, an aqueous dispersion which contains 0.02% by weight of the active ingredient is obtained.
III. 20 parts by weight of compound No. 1.17 are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely dispersing it, an aqueous dispersion which contains 0.02% by weight of the active ingredient is obtained.
IV. 20 parts by weight of compound No. 4.1 are dissolved in a mixture which consists of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction boiling within a range from 210xc2x0 to 280xc2x0 C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely dispersing it, an aqueous dispersion which contains 0.02% by weight of the active ingredient is obtained.
V. 20 parts by weight of compound No. 1.26 are mixed thoroughly with 3 parts by weight of the sodium salt of diisobutylnaphthalene-xcex1-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid from a sulfite waste liquor and 60 parts by weight of silica gel powder, and the mixture is milled in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor which contains 0.1% by weight of the active ingredient is obtained.
VI. 30 parts by weight of compound No. 1.26 are mixed with 97 parts by weight of finely divided kaolin. A dusting agent which contains 3% by weight of the active ingredient is obtained in this manner.
VII. 30 parts by weight of compound No. 1.17 are thoroughly mixed with a mixture of 92 parts by weight of silica gel powder and 8 parts by weight of paraffin oil, which has been sprayed on the surface of this silica gel. A formulation of the active ingredient having good adhesion is obtained in this manner.
VIII. 20 parts by weight of compound No. 1.17 are mixed thoroughly with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.
The action and the rate of action can be promoted, for example, by means of additives which increase the action, such as organic solvents, wetting agents and oils. This allows the application rate of the actual active ingredient to be reduced.
The application rate of the individual active ingredients is varied according to the desired effect, plant species, stage of development of the plants to be treated and agents to be used.
The agents are supplied to the plants mainly by spraying the foliage. Application may be effected, for example using water as a carrier, by conventional spraying techniques using amounts of spray liquor of about 100-1,000 l/ha. The agents can be applied both by the low volume and ultra low volume methods and in the form of microgranules.
The novel agents can be used in application rates of from 0.001 to 5, preferably from 0.01 to 3, in particular from 0.01 to 0.6, kg/ha.
The agents can be applied either alone or as a mixture with other agents or with other active ingredients. If necessary, other defoliants, desiccants, crop protection agents or pesticides can be added, depending on the desired purpose.
It has also been found that mixtures of the novel agents with, for example, active ingredients (A)-(C) stated below lead to further promotion of the desiccant and defoliant effect and help to achieve better control of the undesirable resprouting of plants after desiccation or defoliation (particularly in cotton):
(A) Herbicidal active ingredients from the group consisting of
a. chloroacetanilides, for example 2-chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)-acetamide (common name: metazachlor) described in German Laid-Open Application DOS 2,648,008,
b. substituted quinoline-8-carboxylic acids, for example 3,7-dichloroquinoline-8-carboxylic acid (common name: quinchlorac) described in EP-A-60 429 and 3-methyl-7-chloroquinoline-8-carboxylic acid (common name: quinmerac) described in EP-A-104 389,
c. cyclohexenone derivatives, for example 2-(1-ethoxyimino)-butyl]-5-[2-(ethylthio)-propyl]-3-hydroxy-2-cyclohexenone (common name: sethoxydim) described in German Laid-Open Application DOS 2,822,304 and 2-[1-(ethoximino)-butyl]-3-hydroxy-5-(2H-tetrahydrothiopyran-3-yl)-2-cyclohexen-1-one (common name: cycloxydim) described in German Laid-Open Application DOS 3,121,355,
d. phenoxyalkanecarboxylic acids, for example (4-chloro-2-methylphenoxy)-acetic acid,
e. 3-(isopropyl)-1H-2,1,3-benzothiadiazin-4-(3H)-one 2,2-dioxide, described in German Laid-Open Application DOS 1,542,836 (Bentazon(copyright)),
f. dinitroanilines, for example N-(1-ethylpropyl-3,4-dimethyl-2,6-dinitroaniline described in German Laid-Open Application DOS 2,241,408,
g. imidazolinones, for example 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol -2-yl]-3-quinolinecarboxylic acid (Scepter(copyright), common name: imazaquin); 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-nicotinic acid combined with iso-propylamine in a ratio of 1:1 (Arsenal(copyright), common name: imazapyr); 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl) -5-ethyl-3-pyridinecarboxylic acid (Pursuit(copyright), common name: imazethapyr); methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-p-toluate combined with methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate (Assert(copyright), common name: imazamethabenz) and imazamethapyr (common name; trade mark: Cadre(copyright)), and
h. sulfonylurea derivatives, for example the compounds listed in Tables i and ii below and 1-(4,6-dimethoxypyrimidin-2-yl)-3-(ethylsulfonyl)-2-pyridylsulfonyl)-urea, known as DPX-E 9636.
The commercial products listed in Tables i and ii are known, for example, under the trade names Glean(copyright), Ally(copyright), Express(copyright), Logran(copyright), Setoff(copyright), Muster(copyright), Londax(copyright), Oust(copyright), Classic(copyright), Beacon(copyright), Harmony(copyright)or Remedy(copyright).
i. Diphenyl ether derivatives, such as 5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoic acid described in DE-A-23 11 638 and EP-A-40 898 and its salts (acifluorfen) and ethoxycarbonylmethyl 5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoate (fluoroglycofen) and the diphenyl ether 1-(carboethoxy)-ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (common name: lactofen, Cobra(copyright), 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4trifluoromethylbenzene (common name: oxyfluorfen) and 5-(2-chloro-4-trifluoromethyl)-phenoxy)-N-methylsulfonyl)-2-nitrobenzamide (common name: fomesafen, Flex(copyright), EP-A-3416).
(B) Defoliants and desiccants as mentioned, for example, in G. W. Cathey (1986), Physiology of defiolation in cotton production, in Cotton Physiology (J. R. Mauney, J. McD. Stewart, eds.) The Cotton Foundation reference book series, No. 1, Chapter 14, 143-153, in Morgan, P. W. (1985) Chemical manipulation of abscission and desiccation. In Agricultural Chemicals of the Future (J. L. Hilton, ed.) BARC Symposium 8, 61-74. Rowman and Allanheld, Totowa, in R. Krxc3xa4mer (1989) Erstellung leistungsfxc3xa4higer Kernobstjungpflanzen, thesis at the Faculty of Agriculture of the University of Bonn, and in H. Bergmann, D. Martin (1989), Chemical manipulation of desiccation and defoliation and essential aspects for the application and development of new chemical compounds in the future, in Chemistry of Plant Protection 2 (G. Haug, H. Hoffmann, eds.) 197-246, Springer-Verlag Berlin, Heidelberg.
a. Urea derivatives, for example N-phenyl-Nxe2x80x2-1,2,3-thiadiazol-5-ylurea disclosed in German Laid-Open Application DOS 2,506,690, N-phenyt-Nxe2x80x2-1.3.4-thiadiazol-2-ylurea described in German Laid-Open Application DOS 3,612,830 or N-phenyl-Nxe2x80x2-2-chloropyrid-3-ylurea described in German Laid-Open Application DOS 2,843,722 or the above-mentioned 3-(3-chloro-4-methoxyphenyl)-1,1-dimethylurea (common name: metoxuron),
b. (2-chloroethyl)-phosphonic acid (Ethrel(copyright)),
c. S,S,S-tributyl phosphorotrithioate and S,S,S-tributyl phosphorotrithioite,
d. 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4tetraoxide (Harvade(copyright)),
e. salts of N-(phosphonomethyl)-glycine, such as the isopropylammonium salt (Roundup(copyright)),
f. ammonium DL-homoalanin-4-yl-(methyl)-phosphinate (ammonium glufosinate),
g. magnesium chlorate and sodium chlorate,
h. ammonium sulfate and nitrate,
i. hydrogen cyanamide, calcium cyanamide,
j. potassium iodide,
k. Cu ethylenediaminetetraacetate and Fe ethylenediaminetetraacetate,
l. arsenic acid and its derivatives, such as hydroxydimethylarsine oxide (common name: dimethylarsenic acid),
m. 1,2-dihydropyridazine-3,6-dione,
n. 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid (common name: endothall),
o. 6,7-dihydrodipyridol (1,2-xcex1:2xe2x80x2,1xe2x80x2-c)pyridinium ion as dibromide monohydrate salt (common name: diquat) and 1,1xe2x80x2-dimethyl-4,4xe2x80x2-bipyridinium ion as dichloride or dimethylsulfate salt (common name: paraquat),
p. 3,5-dibromo- or diiodo-4-hydroxybenzonitrile (common name: bromoxynil),
q. substituted dinitrophenols, such as 2-sec-butyl-4,6-dinitrophenol (common name: dinoseb),
r. triazine derivatives, such as 2-ethylamino-4-isopropylamino-6-methylthio-1,3,5-triazine (common name: ametryne),
s. triazole derivatives, such as 1H-1,2,4-triazol-3-ylamine (common name: amitrol),
t. benzothiazoles, such as 2-n-butylmercaptobenzothiazole (common name: butylcaptax), and
u. di-n-butyl 1-n-butylaminocyclohexyl phosphonate (common name: buminafos).
(C) Growth retardants from the group consisting of
a. quaternary ammonium salts from the group consisting of the
N,N-dimethylazacycloheptanium salts, N,N-dimethylpiperidinium salts,
N,N-dimethylhexahydropyridazinium salts, N,N-dimethyltetrahydropyridazinium salts,
N-methylpyridinium salts,
N,N-dimethylpyrrolidinium salts
and N,N,N-trimethyl-N-2-chloroethylammonium salts,
in particular N-2-chloroethyl-N-trimethylammonium chloride (common name: chlormequat chloride) and N,N-dimethylpiperidinium chloride (common name: mepiquat chloride),
b. pyrimidine compounds, such as those disclosed in U.S. Pat. No. 3,818,009 and in Journal of Plant Growth Regulation 7 : 27, 1988 (for example those having the common name: ancymidol or flurprimidol),
c. pyridine compounds disclosed in DE-A-30 15 025,
d. norbornadiazetines, as described in German Laid-Open Applications DOS 2,615,878 and DOS 2,742,034,
e. growth-regulating triazole compounds as described in European Application 88104320.2, in British Crop Protection Conference - Weeds 1982, Vol. 1, BCPC Publications, Croydon 1982, page 3, in Plant Cell Physiol. , 611, in Pestic. Sci. 19, 153, in J. Agron. Crop Sci. 158, 324 or in J. Plant Growth Regul. 4, 181, for example 1-phenoxy-3-(1H-1,2,4-triazol-1-yl)-4-hydroxy-5,5-dimethylhexane,
f. 2-acyl-3-hydroxycyclohex-2-en-1-ones, as described in, for example, EP-A-126 713 or 123 001,
g. 1-(4-chlorophenoxy)-3,3-dimethyl-1-[1, 2,4-triazol-1-yl]-butan-2-one (common name: triadimefon), N-[2,4-dimethyl-5-[trifluoromethylsulfonylamino]-phenylacetamide (common name: mefluidide), 2-chloro-2xe2x80x2,6xe2x80x2-diethyl-N-[methoxymethyl]-acetanilide (common name: alachlor), S-ethyl dipropylthiocarbamate (common name: EPTC) and succinic acid 2,2-dimethylbydrazide (common name: daminozid).
For example, the following mixing partners can be added:
2-Methyl-6-ethylethoxymethyl-2-chloroacetanilide
2-Methyl-6-N-(methoxy-1-methylethyl)-2-chloroacetanilide
2-6-Dimethyl-N-(1-H-pyrazol-1-ylmethyl)-2-chloroacetanilide
2,6-Diethyl-N-(methoxymethyl)-2-chloroacetanilide
3-Methyl-7-chloroquinoline-8-carboxylic acid (salts, esters)
3,7-Dichloroquinoline-8-carboxylic acid (salts, esters)
2-[(1-Ethoxyimino)-butyl]-5-[2-(ethylthio)-propyl]-3-hydroxy-2-cyclohexan-1-one (salts)
2-[(1-Trans-chloroallyloxyimino)-butyl]-5-[2-(ethylthio)-propyl]-3-hydroxy-2-cyclohexan-1-one (salts)
2-[(1-Trans-chloroallyloximino)-propyl]-5-[2-(ethylthio)-propyl]-3-hydroxy-2-cyclohexan-1-one (salts)
2-[(1-Ethoximino)-butyl)-5-[2-H-tetrahydrothiopyran-3-yl]-3-hydroxy-2-cyclohexan-1-one (salts)
2-[(1-Ethoximino)-propyl]-5-(2,4,6-trimethylphenyl)-3-hydroxy-2-cyclohexan-1-one (salts)
2-Methyl-4-chlorophenoxyacetic acid (salts, esters, amides)
2-[2-Methyl-4-chlorophenoxy]-propionic acid (salts, esters, amides)
4-[2-Methyl-4-chlorophenoxy]-butyric acid (salts, esters, amides)
4-[2,4-Dichlorophenoxy]-butyric acid (salts, esters, amides)
2,4-Dichlorophenoxyacetic acid (salts, esters, amides)
3,5,6-Trichloropyridyl-2-oxyacetic acid (salts, esters, amides)
3-(1-Methylethyl)-1-H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide (salts)
3-(1-Methylethyl)-1-cyano-2,1,3-benzothiadiazin-4-(3H)-one-2,2-dioxide (salts)
N-(1-Ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline
2-[4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid
2-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-nicotinic acid (salts, esters)
Methyl-3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]-carbonyl]-amino]-sulfonyl]-2-thiophenecarboxylate (Harmony(copyright))
1-(4,6-Dimethoxypyrimidin-2-yl)-3-(ethylsulfonyl)-2-(pyridylsulfonyl)-urea
2-[-2,4-Dichlorophenoxy]-proionic acid (salts, esters, amides)
5-[2-Chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoic acid (salts)
N-phenyl-Nxe2x80x2-1,2,3-thiadiazol-5-ylurea
N-phenyl-Nxe2x80x2-1,3,4-thiadiazol-2-ylurea
N-phenyl-Nxe2x80x2-2-chloropyrid-3-ylurea
N-3,4-(Dichlorophenyl)-Nxe2x80x2,Nxe2x80x2-dimethylurea
3-(3-Chloro-4-methoxyphenyl)-1,1-dimethylurea
2-Chloroethylphosphonic acid
S,S.S-Tributyl phosphorotrithioate
S,S,S-Tributyl phosphorotrithioite
2,3-Dihydro-5,6-dimethyl-1,4-dithiin-1,1,4,4-tetraoxide
N-(Phosphonomethyl)-glycines (salts)
Ammonium-DL-homoalanin-4-ylmethylphosphinate
Magnesium chlorate and sodium chlorate
Ammonium sulfate and nitrate
Cyanamides
Potassium iodide
Copper chelates and iron chelates,
Arsenic acid
Hydroxydimethylarsine oxide
1,2-Dihydropyridazine-3,6-dione
7-Oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid (salts, esters, amides)
6,7-Dihydropyridol (1,2-xcex1:2xe2x80x2,1xe2x80x2-c)pyridilium ion as the dibromide monohydrate salt
1,1xe2x80x2-Dimethyl-4,4xe2x80x2-dipyridinium ion as the dichloride or dimethylsulfate salt
3,5-Dibromo-4-hydroxybenzonitrile
3,5-Diiodo-4-hydroxybenzonitrile
2-Sec-butyl-4,6-dinitrophenol
2-Tert-butyl-4,6-dinitrophenol
2-Sec-amyl-4,6-dinitrophenol
2-Ethylamino-4-isopropylamino-6-methylthio-1,3,5-triazine
1H-1,2,4-Triazol-3-ylamine
2-n-Butylmercaptobenzothiazole
Di-n-butyl-1-n-butylaminocyclohexyl phosphonate
N,N,N-Trimethyl-N-2-chloroethylammonium salts
N,N-Dimethylpiperidinium salts
N-Methylpyridinium salts
xcex1-Cyclopropyl-xcex1-(4-methoxyphenyl)-5-pyrimidinylmethanol
xcex1-Cyclopropyl-xcex1-(4-trifluoromethoxyphenyl)-5-pyrimidinylmethanol
5-(4-Chlorophenyl)-3,4,5,9,10-pentaazatetracyclo[5.4.1.02,6.08,11]-dodeca-3,9-diones
All-cis-8-(4-chlorophenyl)-3,4,8-triazatetracyclo[4.3.1.0.02,5,07,9]-dec-3-one
Succinic acid mono-N,N-dimethylhydrazide
Ethyl N,N-dipropylthiolcarbamate
N-2,4-Dimethyl-5-(trifluoromethyl)-sulfonylaminophenylacetamide
1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone
2-Propylcarbonyl-5-ethoxycarbonyl-3-hydroxy-2-cyclohexen-1-one
1-(1,2,4-triazol-1-yl)-1-methoxy-2-(2,4-dichlorophenyl)-propan-2-ol
2,2-Dimethyl-4-(1,2,4-triazol-1-yl)-6-phenoxyhexan-3-ol
2,2-Dimethyl-4-(1,2,4-triazol-1-yl)-5-(4-chlorophenyl)-pentan-3-ol
2,2-Dimethyl-4-(1,2,4-triazol-1-yl)-5-(4-chlorophenyl)-pent-4-en-1-ol
2,2-Dimethyl-4-(1,2,4-triazol -1-yl)-5-cyclohexylpent-4-en-3-ol
1-(5-Methyl-1,3-dioxan-5-yl)-4-(1,2,4-triazol-1-yl)-4-(4-trifluoromethylphenyl)-propen-2-ol
Particularly preferred N-phenyl-3,4,5,6-tetrahydroplithalimides are those of the formula I where R is a low molecular weight alkyl radical and A is the group I-1 in which Q is oxygen, R1 is chlorine or bromine and R2 is C1-C6-alkyl. The compounds No. 1.1 and in particular No. 1.17 are noteworthy here.
Preferred application rates for these compounds are from 0.02 to 1.0, in particular from 0.05 to 0.5, kg/ha.
Preferred partners for the mixture are listed in the Table below, where the relevant application rates of the partner of the mixture are also stated. The total application rate for the mixture can be determined from the sum of the amount stated for the tetrahydrophthalimides I and the amount stated in each case in the Table.
The Examples which follow describe methods for the preparation of compounds I and II which have been disclosed in earlier applications not yet laid open. The active ingredients stated in the Tables can be obtained by appropriate modification of the starting materials.